What I’ve Learned From Months of Studying San Francisco Style

Taxiing on the SFO tarmac, I’ve traveled 3,000 miles across three time zones by way of a steel ship in the sky. More remarkable, though, is the feeling that I’ve been catapulted six months into the future, where everything is in beta mode. Billboards for data encryption and cannabis delivery services greet me upon arrival. As per usual, landing in San Francisco reminds me of the first time I took an UberPool here, before they launched the feature in New York: I sat behind the passenger seat, where a man took a phone call, working himself up to a lather over his seed-round funding meeting at a venture capital firm where we’d soon drop him off. After years of spending the odd weekend on the West Coast, I’ve been logging more time in the Bay Area as of this summer, for a confluence of personal reasons. I recently described the experience to a friend as “microdosing San Francisco,” to which they replied, “that is so San Francisco.”

Due to my new-in-townness, I’ve been tasked by Leandra Medine with confirming or myth-busting the notion that everyone in San Francisco wears the uniform of the future: a Dropbox t-shirt and a pair of AllBirds. In the spirit of collecting quantitative data, my brother suggests I go to dinner at a string of nice restaurants (the Morris, Angler, Sorrel, Zuni Café) for a week and count how many hoodies I see. While this strategy sounds delicious, I decide to commit to a different approach: observing the hell out of what goes on around me from my various perches and pedestrian routes. Off the bat, it’s clear that style is not a priority for contemporary San Francisco (and why should it be?), but I press on, curious to uncover the story the city’s aesthetic predilections might tell.

Kindah Khalidy is a painter whose work is flush with optimism. She’s lived and worked in the East Bay for most of her adult life.

An early observation materializes: The generalization of the “tech bro” capsule wardrobe is equal parts provable (look no further than the VC Starter Kit) and not the whole story. With a population that clocks in at just under one million people, the squarish city can’t be pinned down with a single stereotype. Historically, San Francisco has seen groups of all stripes land here and develop a style of their own. It is a city of contradictions, famously a place where people feel empowered to forego wearing clothes altogether.

The hippies of the 60s—impossible to ignore where examinations of this city’s style are concerned—have always struck me as the starting point of San Francisco’s aesthetic sense of self. Before anyone ever uttered the word “prairiecore,” members of the counterculture movement wore 19th century pioneer dress and invented the Victorian-era Wild West aesthetic with the inventory they found in San Francisco’s legendary thrift stores. Maybe the reaction to the tech uniform has been so outsized because San Francisco has long fostered the environment of marching to the beat of your own drum, and a “VC Starter Kit” runs counter to that tradition.

Jillian Knox is an artist and stylist who has lived in San Francisco for eight years. She moved there by way of Chicago, IL and Savannah, GA, and is originally from Washington, DC. This year she’s styled a bunch of cookbooks: from Eat Something by San Francisco Jewish deli Wise Sons, to another on Baja California Mexico which will publish next year. She also just wrapped on Americanized, a short film directed by Erica Eng.

San Francisco Cliques

Beyond the historical influence of the hippies, San Francisco is home to a litany of cultural cliques: there are the outdoorspeople, the tech workers, the next generation of Deadheads. What they all have in common is an aspirational relationship with transcendence: some try to reach it with the Henry David Thoreau approach while others inch closer with alternative music or by channeling Steve Jobs’ particular brand of reality distortion, aiming to push the limitations of our world through disruptive ideas. These archetypes set the city’s tone.

Which is to say: It’s not a very dressed-up place—a mood I clocked right away coming from New York, where looking informal or laid-back wasn’t typically my goal. I think the Bay Area’s relaxed posture is informed by a convergence of factors: There’s the lingering, liberal attitude of the 60s counterculture movement, pulsing quietly and course-correcting the culture when it gets too uptight. There’s the city’s proximity to nature (hiking trails, humbling redwoods), which rewards the person prepared for anything—a midday hike or bike to blow off some steam, a trip to Big Sur after work on a Friday, an off-site vision quest. The year-round season-less forecast is both temperate and tough to predict, as sunny or chilly or foggy microclimates hide in the slant of the hills. You pretty much always need a just-in-case fleece or sweater.

Because of the Bay Area’s thin membrane between town and country, Patagonia baggie shorts and leggings and normcore Outdoor Voices Megafleeces are acceptable everywhere. They’re not compartmentalized by activity or time of day the way they are in New York. (Anytime I arrive somewhere thinking I’m underdressed, someone else relieves me by showing up a notch more casual.) Tech recruiters wield this like capital, touting lax company cultures in order to win over the brightest minds in a competitive hiring pool. Style in San Francisco lacks the pretension that funnels down from New York’s lifeblood (finance), though I’d be naive to assume that that pretension doesn’t find a place elsewhere. In fact, in San Francisco, there seems to be more currency in appearing casual than there is in appearing affluent.

Torryne Leigh Dunlap Choate is a florist, ceramicist, visual artist, and music enthusiast whose floral design studio, Birch, has held court in Hayes Valley for years. Born in San Francisco in 1968, Torryne moved back in 1991. She’s now lived in Hayes Valley for 28 years. “SF style can be an oxymoron for the general population,” she tells me, “However, there are still folks who make a concerted effort to develop their own style. I am fortunate to call these people my dear friends. West Coast casual turned up to 11.” Torryne has a tabletop ceramics collaboration with Ubi Ind Denim and food stylist Jillian Knox launching soon.

Consider the Patagonia Better Sweater vest, available in a range of gravelly colors: It’s outrageously popular here—almost an icon in its own right. (New York is not exactly immune to the fever, either.) It may look familiar to you if you have an HBO subscription: Silicon Valley shows the Pied Piper payroll as a slovenly, ragtag crew, outfitted in the vests and zip-up hoodies. In the last year, there’s been no shortage of costume designers recreating the sartorial whims of the Bay Area onscreen, but many are broadening an outsider’s idea of what dressing here can look like. Across the bay in Oakland, Tessa Thompson wears earrings that could double as subtitles for Boots Riley’s Sorry to Bother You (designed by local artist J. Otto Seibold), and in Beautiful Boy, Steve Carrell and Timothée Chalamet drive between Marin and the Upper Haight in chamois shirts and hempy tees. The Last Black Man in San Francisco, meanwhile, focuses its lens on Jimmie Fails, skateboarding in and out of Hunter’s Point clad in his uniform of a red flannel shirt, chinos, and black Adidas Sambas.

As with any city, there are as many people who fit the archetype as there are outliers.

The Outliers

I’m still getting to know the city geographically and socially (and culturally and sartorially and meteorologically), so I’ve attempted to glean some perspective by photographing the style of a sample set of Bay Area residents whom I’ve met through one or two degrees of separation (their photos are seen throughout this story). I also make note of anyone who debunks the reigning stereotypes of San Francisco style.

Marie-Clare Treseder Gorham is a folk artist who has been on the Bay Area periphery since infancy. Recently she’s been doodling some spooky folktale characters for an upcoming letterpress collaboration with artisanal print shop The Aesthetic Union in the Mission. Gorham says the city’s style has shifted substantially since the days of her youth where she’d carpool in, anxious for Haight Ashbury’s unrivaled vintage. “Today, the city’s vintage scene is single-handedly kept alive by Cindy Spade, of Ver Unica,” Gorham asserts. She notes that not all hope is lost: “There are always a couple of cool cats around the corner.” She drew and designed this dress while pregnant but continues to wear it postpartum for comfort. It’s covered with medieval monsters, “influenced by chimaera from ye olden-timey days,” and was sewn by her longtime collaborator Nancy Bui, owner of North Beach Tailoring, SF.

One morning, there’s a girl sitting next to me at a coffee shop, studying for a standardized test in a yellow bowling shirt: It says “Frank” in looping, cursive embroidery. I spot an older woman at a toast joint in a red Kangol bucket hat, and another customer wearing shaggy, red crossover slides reminiscent of Muppet feet. Walking on the Embarcadero, I pass someone wearing a “FarmVille 2” t-shirt and can’t believe my luck. On Fillmore, I see a girl disembark the bus, almost in slo-mo like that Royal Tenenbaums scene when Nico’s “These Days” plays. She’s wearing a muslin-colored top that reminds me of Orseund Iris’ most Victorian blouse. Later I happen upon the clerk of a comic bookstore wheeling a clanky cart of graphic novels outside, the gold hardware on her black overalls gleaming in the sun.

Pockets of the city, where clothes look like a means to an end, catch my eye. By Ocean Beach, there’s the Outer Sunset, where Trouble Coffee and the surf shop Mollusk have shored up. Known for its cinnamon sugar toast and “thrash or die” coffee cups, Trouble sees a steady current of beanies, athletic shorts, and mid-calf socks whiz by on skateboards. Mollusk’s stocked with fisherman sweaters, barn jackets, and henleys, for those not in the market for a wetsuit and sex wax. Further inland, bakers in black t-shirts covered with flour at Tartine Manufactory and Josey Baker Bread’s The Mill knead dough with their hands and seem to ride a wavelength opposite to the city’s technologists.

Making weekend plans with friends, no one ever floats the idea of shopping as a worthwhile way to spend an afternoon. (Fine by me.) Unsure of where I’d go to find it, I suspect that Lisa Says Gah’s following is much more robust outside of San Francisco than the fanbase within the city limits. In the Castro, a local menswear shop known for its raw denim, wide wale corduroy, and Carhartt canvas called Unionmade recently shuttered. Julie Wainwright founded The RealReal in San Francisco eight years ago; I wonder how much foot traffic its SF-based consignment shop sees? While San Francisco’s not the monoculture or meme it’s made out to be, it’s fair to say that clothes aren’t topping the charts when you consider the ways this city radiates beauty.

Artist Jenny Sharaf has lived in the Bay Area for 12 years, and has noticed a shift as the cost of living has driven creatives out of the area: “San Francisco definitely used to have better style, as a whole. More artists. More bohemians.” She maintains that the city still has some of the best vintage stores in the world, though. I love Sharaf’s paintings—they’re gigantic and gloppy, which I mean in the most complementary way. She’s like the Michelangelo of spin art. When I visited her studio, she was getting cracking on a new book project, and she’s launching a new edition of risographs this month.

Late one afternoon I have to head a few miles north, at an hour when the light makes everything feel sacred. Suspicious of motorized scooters and with no driver’s license to my name, I consider the ride-hail an occasional and necessary evil. A driver from Greece, with a 4.8 rating and a Gray Ford Fusion, picks me up.

We’re silent for a while. At some point, he slows for a speed bump and pauses to look up at an imposing, four-storied Victorian on the corner of Alamo Square Park. (Later, when I look it up, I read that the house has had many lives: First built by a German confectioner, it changed hands in 1928 when Czarist Russians transformed the basement ballroom into a nightclub called “Dark Eyes.” In the 60s, commune members performed Satanic rituals there and kept a lion cub in one of the towers, its claw marks still visible on a door frame.) Accelerating as we pass by, the driver asks me if it’s a house. I tell him I think so. Braking for a stop sign, he shakes his head in disbelief. “Wow,” he says, “I think San Francisco is the most beautiful city in the world.”

Post-script: Because it’s hard to write about the beauty of San Francisco without acknowledging its social challenges, here’s a comprehensive list of non-profit groups that need volunteer help or donations of specific items.

Photographed by Edith Young.

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